Are you making these email mistakes? Here’s how to fix them.

Chess in Brooklyn

A few weeks ago I met up with a good friend of mine over wine and dinner and we got to talking about email–the number one form of communication we all use, and the fact that so many of us could do it a lot better. If you use email or any other digital medium, chances are you’re writing far more than you think you are–and your writing is what represents you.

Email is writing, plain and simple, and it often gets us into trouble.

Amber and I chatted about email, and what mistakes people often make, and how to fix those mistakes through better writing (and strategic thinking) to improve your professional (and personal) life. She was fascinated with the writer’s workshop, so over the course of a delicious glass of wine (or perhaps two), I shared with her nice ways that people often make mistakes in email. (To see the original essay, check out the Fast Company article featured earlier this Fall):

Here are nine common mistakes you might be making:

1. Sending emails only when you need something.

The best time to build any relationship is before you need something, not waiting until the moment you need something. A friend of mine gets into the habit of sending five thoughtful emails each Sunday night to check in with people who he likes, admires, or thinks of. An email might look like,

Hey, saw some great news about you—just wanted to say congratulations! I love watching what you’re up to through my various news feeds, and I wanted to send a note to say how much I hope you’re doing well.

It’s a great way to remember to reach out to folks you want to be in touch with, and an actionable way of practicing gratitude.

2. Forgetting that there’s a person on the other side of your email.

Just as you wouldn’t walk into a friend’s house for dinner and bark out a command, often those little niceties in the intro and end of a message can go a long way. Social cues aren’t dated constructs; they’re valuable warm-up phrases in communication. Start by saying hi, comment on someone’s latest achievements, and wish the other person well.

Hey stranger! It’s been a long time. If Facebook’s telling me the scoop, it looks like you had an eventful Spring…congrats on all of your successes!

3. Using the first person too much.

Many emails–and essays–are written exclusively in first person. Shift the focus to the recipient and consider what they want, need, or would like to hear. After writing an email, scan it quickly for how many times you use the word “I.” See if you can edit some of them out.

For example: “I’m teaching a new writer’s workshop this Spring, and I want help sharing the program. I think you’d be interested in it” (all “I” statements) can be turned into:

Hey, Leslie. A while back we chatted about ways to improve your writing skills–I wanted to reach out about this writing workshop for creatives that’s just launched. I thought you might enjoy taking a look. Let me know if this is what you were looking for.

4. Sending the email at the wrong time.

Just because you’ve written it now doesn’t mean it needs to be sent at this exact moment. Delaying the send is one of the most powerful and underutilized tools of emailing.

Evaluate whether or not the message is urgent and needs to be replied to immediately. If you’re cleaning up your inbox during your scheduled time, fire off the messages that are urgent and consider sending messages in the morning.

Scheduling emails to be sent in 24 or 48 hours gives you (and your clients) space to breathe between nonurgent projects, and it also sets up a rhythm of communication whereby your client no longer expects you to reply instantaneously. The more structure and parameter you give to the form of your messaging, the easier it is for the client to learn what to expect. You can either train someone to expect instantaneous answers at all times, or to learn the rhythm that’s best for you and your business.

Then, in the case of an emergency, if the client emails and you need to solve the problem straight away, you can send a quick message late in the evening or on a weekend. In this scenario, you become the hero to your client.

5. Sending to too many people.

More recipients in the “To” field does not mean that you’ll necessarily get more answers. In the age of digital marketing, people who blast messages in broadcast form without understanding who is in the “to” line can erode their chances of a message being opened. A perfect email is one that’s sent to exactly who it needs to go to, with a specified desired outcome.

The more specific you can be about who you ask, the better. Asking everyone in your network is bound to get you a bunch of silence in our overconnected world, or unsubscribes and un-follows across your various platforms. It’s better to ask three people who are very well equipped to answer your query than 15 people who aren’t interested at all.

The more specific you can get about who should be receiving the message, the better. One direct ask that results in a yes is better than asking 50 people who don’t respond (and spamming their inboxes).

6. Knowing nothing about the person receiving your email.

Do your homework on the recipient. One great tool to glean fast information about who you’re talking to is Rapportive, a sidebar that lets you see the latest public posts (and a picture) of the person you’re communicating to.

7. Forgetting to send updates or interim messages.

If you’re waiting for an important message from someone, the time spent waiting for a delivery can seem interminable. If there’s a long delay in sending an item that’s highly anticipated or expected, or you’ve experienced a few hiccups–send a one-liner email to update your receiver on the status of the project. You’ll know that you need to send a quick note when you start to get anxious about not delivering or they seem to be a bit flippant.

Sample copy:

Hey, Sarah. Just wanted to send a quick update about the delivery of our proposal. We’re set to get you something by next Friday, but we might be a few days early. Talk to you next week! Let me know if you have any questions in the meantime.
Hey, Sarah. I know we touched base last month and I’ve been far too slow in getting back to you. I’m still working through the pile on my plate, but I should have something in the next 2-3 weeks. Didn’t want to keep you guessing! Talk soon,

8. Making messages too long.

Depending on the nature of the message, emails can vary from a few words to thousands of words. The longer the email, the less likely that someone will read the entire thing. Long emails generally mean that a larger strategy, framework, or document might be in order. Some companies shift to using four-sentence emails and linking to longer pieces of work through Google Documents, Asana, or Basecamp (or other project management software).

9. Using email exclusively.

Efficiency does not necessarily mean one single system. Often, redundancy in communication can be extremely helpful, as each tool (video, chat, email, Skype) adds a layer of human nuance back into the correspondence that’s happening. Laura Roeder’s digital marketing team is distributed across multiple countries, and in order to stay in touch (and in concert with each other), they focus on “over-communication,” through the use of multiple tools at once.

Now: Four ways to focus on writing better emails:

  • Tell sticky stories. Everything makes more sense with an illustration. Highlight and example, illustrate an ideal customer avatar, or tell a specific instance of a problem you had. Setting the context and the stage (that seems obvious to you, the writer), makes it easier for people to understand the pain point, the context, and the reason why you’re writing. When people can see your story–who you are, where you come from, why you’re doing what you’re doing–it’s easier for them to become a part of it.
  • Use the four-sentence, one-link rule: Keep your email to under four sentences (or five!). Focus on the pain point or problem you’re solving. Limit yourself to only one link. If you have to, make that link a document.
  • Be responsive and reflective: Observe how others communicate and adapt your style to meet them midway. Customize your communication by mirroring the style of a received message. Does someone send short messages with formal addresses? Respond in style.
  • Bookmark emails that you love with Evernote. Use the vast number of emails in front of you (and in your inbox) as clues to great messaging. Watch what emails you open first and are most excited about. Create a few folders in your mailbox system for great introductions, sample short messages, and thank-you notes that you like. Keep these for future use if you’re ever in a bind. In any art, there’s no need to reinvent the wheel–and paying attention to great writers (and what we personally enjoy) is a great way to get started.

Email is our number one form of communication, which means that everyone is a writer. The most powerful thing you can do in both your personal and business life is learn how to write well and tell great stories. Messages that persuade, content that converts, and language that inspires action are critical for getting what you want.

What do you do? What hacks do you have to make email better (and more bearable) for everyone?

The hidden power of doing interviews (and how to get better at them).

New York Building Fronts

I used to hate interviews. I stammered, I inserted words such as “like” and “um” a whole bunch, and my voice pitched up at the end of nearly every sentence.

I sounded exactly like what I was—a young 20-something female with insecurity about my ideas.

Then I started listening to the interviews and analyzing them. I paid attention to everything—from the sound of my voice, to the way it pitched up, to my breathing, looking at the construction of sentences, and trying to understand the moments when it felt like I got insecure versus when I was the strongest and most confident.

Each time, I focused on something I could improve. My voice lowered, which made me sound more confident and also feel more confident.  I slowed down. I added more breath, which built calm. I layered back in some room to giggle and rush through my words, because when I get excited I speed up—and I like that authenticity. It also occurred to me that I like doing interviews at a particular time of day—early afternoon, when I’m starting to feel very chatty and I want to talk to people. I started scheduling them for times that fit well with my brain schedule.

Getting better at interviews.

To get better at interviews, and presentations—the best way is to do them over and over again.

Grab a friend (or a video) and set yourself up with a mock interview. Chat for twenty minutes. Share your ideas. Let yourself ramble. Then, watch the tape. Ask for feedback. Where were you your best? What made you shine? What parts could improve? Work out each of the little stumbles until you feel comfortable with the sequence of changes.

Find out what makes you feel good. Set up a room, an environment, a location that you love. Maybe you scout out the person beforehand. Maybe you have your favorite cup of coffee–and your favorite glass of wine before hand. Maybe you need to warm-up to conversation with a trusted friend before you start.

Perhaps you write out ideas in advance so you have a cue sheet or you’ve done some advance thinking. I like to ask my interviewer for a general topic list and sample questions so I know what area(s) we’ll be chatting about. Sometimes I’ll write out an essay answer the night before to the questions–and while I won’t read it out loud the next day (it sounds terrible on tape, FYI), just the act of doing the thinking helps set me up for good stuff later.

Learn to love the process: self-reflection and being able to identify how to make changes is powerful.

Why I love interviews.

Now, somewhat surprisingly, I actually enjoy listening to the interviews I get to do.

Beyond the technical considerations and feedback, it becomes a place to test ideas and learn from the medium of voice. For some reason, the way I explain things out loud is different than in print—and so the spoken word becomes a place for me to learn more about my thoughts.

Listening to interviews is a chance to mine your mind for thoughts and ideas, and write out some of the ways you construct sentences, thoughts, and observations. You can pay attention to when you get excited, where you stumble, what you get frustrated or stumped by, and what comes easily to you.

A good interviewer will ask thought-provoking questions, and often I’ll stumble into a new area of ideas that I haven’t written about yet, yielding juicy content and rich ideas for future essays. I discovered that the ideas we unearthed were seeds waiting to be watered, new ideas to plant. I still love writing far more than I love interviews. I prefer to be alone, with my thoughts and ideas, sharing my brain through this pen-and-paper medium. When you read my posts and my books, you get my brain.

But interviews can be potent sources of discovery and idea generation.

This week, I was interviewed by Joel Zaslosfky over on the Value of Simple podcast. We talk about identity, how difficult it is to define yourself and what you do, the drawbacks of storytelling, and the power of addiction in both positive and negative terms. If you have a half an hour today, download it and take a listen and let me know what you think.

The art of asking: 21 ways to ask for what you want and get it.

Vulnerable-700

“If you don’t ask, the answer is already no.”

What does it take to ask for what you want—and then get it? There seems to be a magical art behind creating a great ask, and we all know stories of people who seem to get exactly what they want whenever they ask. Magicians who bend and will the world to their ways. Why is this? What are they doing that no one else seems to be doing? How do they ask for what they want and seem to get it every time?

Culturally, it’s not always the norm to ask directly for what you want—or we do a terrible job of it (and women are worse, according to the New York Times). Instead os specifying what we want, we hem and haw about ideas, often walking away from great conversations without clearly articulating our message, what we hope to achieve, and how the other person can directly help us.

Creating a great ask (and learning the ability to say no) are two skills that successful people learn how to do really well. In the past decade, some of the things I’ve asked for and negotiated for include: asking for multiple raises and getting them consistently, negotiating salary bumps of 20% or more (with credit to Ramit Sethi’s persuasion tactics), winning over $50,000 in scholarships (competitions and essays were involved), and recently raised $33,000 for charity: water by promising to swim naked from Alcatraz to San Francisco if we raised enough money.

In addition, I’ve helped clients understand persuasion tactics and develop scripts to ask for what they want, including the delicate art of deciding to do it anyways and asking for forgiveness rather than permission. Several people asked me to collect my notes on how to ask and share them publicly. Here are my top tips for creating a great ask—in order to get more of what you want.

The art of asking for what you want: Part 1: You have to actually ask.

1. First, know what you want. This is an all-too-obvious step that’s often overlooked. Often it’s not always clear to you (or others) what it is, exactly, that you’re in need of. The more clarity you can have about what you want, the better. Take the time to learn, figure out, or discover exactly what you want. Once you know what you want ($1M in funding, a date with a lady, a new bookshelf, a corner grocery store), it’s easier to ask for it.

2. Ground yourself in why you’re doing what you’re doing. Start from the heart center: before I ask others to join or respond, I check in with myself, asking with my heart and mind and body, making sure this is what I want and that it resonates with who I am and what I stand for.

Is this something that I want to do, and want to do deeply? Is this something I stand for and believe in?

If you don’t want it at the center of your core, ask yourself why you’re going after it. If you do want it, ask yourself what you’d be willing to do for this. Much of my work is contingent on confidence and alignment with the programs I’m creating. If and when I draft an email that doesn’t “feel right” or my intuition tells me is coming from a place of loneliness, desperation, or need—I pause on the email and draft it a few other ways.When I circle back and remember why I’m doing what I’m doing, the words come more easily.

Amanda Palmer, in the highly watched (and just as readily criticized) TED talk, speaks of the vulnerability that is required in asking for what you want. To ask for something is human; to want something and ask someone else for itrequires a connection.

“Through the very act of asking people, I connected with them. And when you connect with them, people want to help you. It’s kind of counterintuitive for a lot of artists — they don’t want to ask for things. It’s not easy to ask. … Asking makes you vulnerable.”

— Amanda Palmer, The Art of Asking

3. You have to actually ASK for what you want. It sounds so simple to write this, and almost insanely easy advice. But there are too many people who do not ask for what they want. They’ll tell you a story, email you to say hello, spend hours talking in circles about their idea, hedge and hum about a faint aspect of their idea—and somehow hope amongst all the befuddlement that somehow the other person they are talking to will be able figure out what is is you want and help you solve your problem.

In order to get what you want, you have to ask for it.

4. Be direct, clear, and specific about what you want. Make it ridiculously clear what you’re asking for. Be direct about what you want, who it’s from, and when you need it, and what a desired outcome looks like. The more specific and direct you can be, the better.

  • Define the problem. What are you trying to solve?
  • Specify what it is, exactly, that you want. What materials, processes, steps, pieces, or people are involved to solve it? Is this made abundantly clear–and easier to read than an IKEA assembly manual?
  • Outline how much time, energy, money, or commitment you think it will take. Be clear about what the person will have to do to fulfill the request. If it’s a sale, specify when, where, and how they can get what you’re asking them to by. There’s nothing like deciding you want something and realizing that the person who invited you didn’t put a “buy here” button on their website.
  • Be direct. Put the ask up front and early, and again in the close of the message.

5. Be selective and targeted about who you ask. The more specific you can be about WHO you ask, the better. Asking everyone in your network is bound to get you a bunch of silence in our over-connected world, or active unsubscribes and un-follows across your various platforms. It’s better to ask three people who are very well equipped to answer your query than 15 people who aren’t interested at all.

Do not send your email to your entire contact list. People in Boulder have no interest in the program you’re teaching in San Francisco (unless, perhaps, it’s a digital class). The more specific you can get about WHO should be receiving the message, the better. One direct ask that results in a yes is better than asking fifty people who don’t respond (and spamming their inboxes).

This can be far more work than it sounds. When I craft campaign emails and fundraising emails, I’ll sit and pour through my contact database and customize a list of 20, 80, 100, 200, or 300 people that I think would actually be interested in my project and that I feel comfortable emailing. Sometimes I goof and send people too many messages, but thankfully most of my friends and colleagues have been forgiving and kind about the messages I’ve sent (and say no when they want to). I’ll craft 10 different versions of emails to go to small sub-groups of twenty people, each group carefully constructed based on who knows who; what the question is; what the story lead is; and how I’m framing the ask.

6. Use social proof by creating micro-groups and mini-masterminds. When you email a small enough group, the presence of one initial response often prompts others to respond as well—creating the inertia of ongoing conversation rather than having to circle back and bother more people. When I email a group of five people that I highly respect and ask them to join a conversation, I try to include someone that I know is great at responding quickly. This generates an ongoing conversation.

When the group is small enough, the conversation becomes private and personal enough that it’s like a micro-mastermind group with content rich enough to be worth thousands of dollars. Sometimes after an day on a message thread, people have written back to me privately and said, “this advice is worth gold—thank you so much for including me in this group. I learned so much!”

An example that stitches these all together:

A while ago I ran into a problem with a particular type of client that I was having trouble closing—and instead I ended up spending weeks in back-and-forth emails continuing to describe the product instead of making the sale (and ideally directing my correspondent to a solution to his problem). I couldn’t figure out if this was a dead-end lead, or if my writing was generating the excessive conversations.

I thought—why don’t I ask a few of my successful business friends for advice?

I thought closely about who might be a good person to answer the question, directed an email at three people, copied each of them on a single email, and wrote the following request:

A sample script for asking a mini-team of experts for help with a problem:

Dear John, Susie, and Rob:

I hope you’re well. I’m having a pinch point in my client pipeline and I’m looking for some feedback—and I think you’re the perfect person to help me out because I’m pretty sure you’re a pro at dealing with this type of client request in your business.

This email will probably take you about 10-15 minutes to read and respond,and I’d be incredibly grateful for your straight-up advice. I’m predicting that you know exactly how to deal with this problem, which is why I’m contacting each of you.

If any of you are swamped today or in the middle of something that needs your attention, feel free to delete this email or send a quick “so sorry, can’t,” so I know not to bother you again. Ideally, you’ll know a great resource (a book or link) that answers this problem and can think through this quickly with me. Many thanks for your brilliance in advance.

Here’s the situation: … I’d like to come up with a great response that changes the answer I’m getting (below) into an answer that converts into a sale. This email chain below is a typical one for me … (and here you continue to describe the email you get and copy, exactly, the messages you get and the emails you’ve sent previously.)

In summary: when I ask people for help, I select one or a few targeted people to reach out to, I define the problem, outline what I’d like them to help me with or what I’d like them to do for me, and tell them how much time I think it should take, and I give them enough information to make it easy to answer. As a courtesy, I also like to let folks opt-out if they’re in a busy point in their lives.

Art of Asking


Part Two: How many times should you ask?

7. Make sure you ask in multiple ways and in multiple places—show up across multiple platforms customized for different individuals. Every time I launch a program, offering, or class, I make sure to send my “ask” into the universe in a number of different ways.

It’s not enough to create something and wait for people to show up. Both before and after you make your product or offering, you need to invite people to come take a look, to review it, to purchase it, and to see what you have to share. Without asking people to buy your product, it’s like walking into an empty room, filling a keg with beer, and not telling anyone you’ve got beer behind those brick walls. Unless you put a sign on the door, distribute flyers in all the neighborhood mailboxes, and put a sign out front with free beer coupons for the first 100 customers, no one will know that there’s a keg full of delicious goods inside of that brick house.

You need to show up where the people who have what you want are already playing, paying, or talking.

“It’s not enough to create something and wait for people to show up. You need to tell them about it.” (Tweet this!)

Put your offering or request in several (targeted) places. Show up in person, on email, in newsletters, on twitter, on Facebook, and in any other place where people who want what you have—or can give you what you want—already spend time. Further, you’ve got to ask in a number of different ways.

Next, send personalized requests or invitations on a 1:1 basis to people you think would be great early adopters, fans, or supporters. Tell people what you’ve been up to. Start with your own network, no matter how big or small, and ask them to come show up. An email to ten friends and family members asking for support is more meaningful initially than spamming your entire Facebook friend list and showing that you’ve invited 500 people and only 2 of them RSVP’ed.

8. Ask multiple times. Do not be afraid to ask someone more than once for something.

Sometimes I get nervous that I’m repeating myself. Remember that what you hear is not what they hear. The last time that I got nervous that I was talking incessantly about my project for charity: water, I started to get sick of my own voice and assumed everyone else was tired of hearing about the project, too. In reality, you’re only talking to each person once or twice, even though you yourself have had the same conversation hundreds of times. Keep going and remember that each time you ask, the person on the other end may be hearing you for the first or second time only— and every time you ask, you increase your chances of getting what you want.

Additionally, people generally need to see your ideas 4-7 times before they really familiarize themselves with it. Multiple messages are okay. If you send one email and no one responds, you might need to send another message in two weeks’ time, after people have had a chance to see it and hear about it. Just because you are talking about it all the time does not mean that the other person hears or sees everything you’re saying.

It’s okay to ask more than once. I imagine that some folks are scrolling their iPhones while on the toilet, reading in line, and not always ready to act or do something at the moment and place where they receive your message. In a mobile world, people are getting messages while they are already busy—out shopping, eating, running errands, or at work. They want to donate or buy, but forget. Following up with a second ask is certainly fine.

And if you create a great story—and you sweep people up in your project, they will rally behind you and want to know how the campaign is doing, and they want to know when you win. People love a good story. The additional messages aren’t a nuisance if they’re well-crafted—they’re bringing people into the story and along for the ride. Share your enthusiasm with them.

9. Try asking EVERYONE. Push yourself beyond your comfort zone and strike up conversations with strangers. Talk to your taxi cab driver, your bus driver, your school teacher, your yoga instructor. Tell your story like it’s the only story you have. (Note: this differs from targeted asks, above, because you’re not sending a blanket email to everyone that’s non-specific. This time, every person you meet should be someone you can talk to about your project and process, and each person should get a targeted message or a variant of a custom message).

When I was on a mission to raise money for charity: water, I asked my bus driver, my taxi driver, the brunch group, people at my swim, the coffee barista, and every friend I knew to participate. I ended up having one of my Lyft drivers laughing so hard that he gave me cash straight out and volunteered to graffiti-paint my body for the swim.

You. Must. Ask. Everyone.

10. Practice over and over and over again. Every small ask is practicing for a bigger ask. Each email and correspondence is an opportunity to practice. In college, my swim coach set us out on missions to experiment with our psychological edges—and in one experiment, we had to ask for a free lunch. It was awkward. Many people said no. And some people said yes. Each time, we practice asking for unusual things.Ask until you get a yes answer. Learn from each iteration.

11. Follow up. Ask. Do what you say you’re going to do. Say thank you. If you want to stand out, ask for what you want, follow up, and follow through.Most people don’t do this.


Part Three: The psychology of decision making, why touch matters, and considering context.

12. Be audacious. Much like Jia Jiang’s experiment with hundreds of rejections (where he set out to get used to the idea of rejection by asking for ridiculous things), he found that the more he asked, the easier it got to ask for what he wanted. As a bonus? People said yes. He ended up driving a police car, flying a helicopter, and dozens of other crazy adventures simply because he walked up to people and had the audacity to ask.

13. Keep it simple. Put the ask on the table. Make it easy to find. Make your wishes known.

  • Give alternatives if you’d like, but stick to two, maximum three. Sometimes it’s easier for people to say yes to one of two options rather than having to choose between many. Stick to just one or two things.
  • Start with small wins.Ask incrementally for specific, small things. Get a foot in the door. Don’t ask for the big thing until you’ve established rapport, responsibility and demonstrated follow-through with someone.

14. Pay attention to context and surrounding cues. People make decisions based on their physical surroundings–much more than they would probably believe. Of all the senses, touch is one of the most important contextual cues. Researchers think this is because we develop our sense of touch first, as infants. According to The Economist, on decision-making, “research shows that our choices can depend on whether we are holding something heavy or light,” and “it seems our minds take many physical metaphors (such as heavy or light, soft or hard) literally.” Bring someone a warm beverage and have them sit on a hard chair, and see what happens with your negotiation or ask.

15. Ask at the right time: understand how (and when) people make decisions. If you are asking for something complicated and difficult, ask before the well of will-power is depleted. People grow weary of making decisions throughout a days’ time, and make better choices (or are willing to decide at all) in the morning, or when they are fresh (see more on decision fatigue in Psychology Today). In the evening, you’re more likely to get a “no” as a response if the person you’re asking is tired and worn out from a long day. 

16. Be confident in how you ask. Make a statement, hone your pitch, and then put a clear request in at the end.

If it’s a verbal ask, don’t let your voice trail off at the end. Practice body and vocal confidence by standing tall, shoulders back, and with your head up in a controlled, confident stance. If you don’t feel confident about what you’re asking, chances are you need to check in and make sure that you believe in your product or offering, and you need more practice.

This is a great time to fake it until you make it.

17. Master the Pause. When you ask, look the the other person in the eye. And—this is the most important part—then shut the fuck up. Ask, simply, and then wait. Don’t throw a bunch of garbage words into the space between your ask and the person’s response. The waiting part—that silence—is deafening, but critical.

Give people space to consider what you said and respond thoughtfully before jumping in to fill the silent space with more words. Make a simple ask, and wait. Let them make the next move. Much like kissing a guy (or gal) for the first time, the sweet spot is in the pause and the time where the two parties consider each other.

If you speak up too quickly, you can push them into a space of no.

Body language is critical for this step. Assume a positive stance (feet hip-distance apart, casual, standing still);and put your hands in a neutral position (by your sides or with both hands touching in front of you, loosely). Keep your chin up and your heart space open. Smile confidently and look them in the eye.

Too many people shoot themselves in the foot by asking for what they want and then immediately layering in a couched response that assumes the person on the other side doesn’t want what you’re offering.

Assume that the person you’re asking would be delighted to help you, has exactly what you need or wants precisely what you’re offering, and that they’ve just been waiting for you to ask them.

Surprisingly, I’ve had multiple encounters where people write (or say) in response, “Sure! That sounds great—I’ve actually been looking for a writing workshop, thanks for thinking of me,” or “Absolutely, I’d love to help—I know just the right person, want me to set up an introduction?”

Yes, yes I would.

It’s surprising how much we don’t get when we don’t give people the opportunity to help.

An ask is a connection. It’s not about having another person go to great lengths for you. It’s about creating a scenario where someone who wants to give can match with what you want.

“Asking is about connection. Create a space where people can give and you can receive (and vice versa).” (Tweet this!


Part Four: Avoid terrible asks, be kind, and make sure you say thank you.

18. Avoid terrible, generic, vague asks.

say no to many of the requests for coffee and lunch dates that come my way—although not always—largely when I’m not sure if I can be useful or if I already know that I need to dedicate that limited time to my existing projects and processes.

The worst type of ask is when someone says “I’d love to pick your brain and get your (generic) advice—do you have time to have dinner or get together one day?”

This is non-specific, non-limited, non-structured, and I’m not sure what I can help with or how I can be useful. Chances are that I’ve already answered some of the basic questions in one of the hundreds of essays I’ve written before, or that I can recommend a book or a process that can be helpful and easily sent over in a minute—if I knew the nature of their problem. Lastly, I want to know why it is that I, specifically, am useful–what is it about me that can help you more than anyone else?

When I get these emails, my reaction is to run and hide and shout, NO, NO, NO!

Luckily, I don’t say that. Instead, I write back and ask for a bit of clarification. It’s never a problem to ask people to do a bit more work before you help them. Here are two great scripts for saying no—and helping someone focus their ask:


A sample script for saying no to nonspecific requests for your time:

There are two great ways to respond to nonspecific requests for your time:

Question 1: “Can I ask you a quick question over lunch and pick your brain?”

Answer: “If it’s a quick question, send it my way right now and I’ll answer it quickly! If it’s a longer conversation you want to have, my lunch hours are reserved for clients right now, so you can book time with me here [insert link to your consulting page].” (Hat tip to Marie Forleo and Laura Roeder for this gem.)

Question 2: The vague “I need help and I’d love your advice … ” that generally ends with an ellipses “…”

Answer: “Hey–Thanks for your email. The more specific you can be in your question, the easier it will be for me to help you. Would you put together a list of specific questions you’d like to have answered and I’ll see if I can pull together a quick set of resources and links or point you to the right place?”

To be clear: I’m more than happy to answer questions that are specific, clear, and direct. When people email me a question like this:

“Hey Sarah, I loved the book you mentioned at the Writer’s Workshop on Storytelling and the Hero’s Journey, but I forget the name of the title. Mind sending it to me again?”

It’s EASY to answer. In fact, I find these questions so useful that I typically develop resource pages for specific topics (like storytelling), along with a custom ‘Canned Response’ template in my Gmail system so I can just drop a response in an email and fire it over quickly. I love questions that are easy to answer and quick to send over, and create a lot of value for the recipient.

And as a side note: when people ask you questions, it’s a great clue into what people think you’re good at and what services people want your help answering. I’m grateful for all the emails I get because when I take the time to respond to one, it usually generates a blog post (like this one, in fact), where I can develop a list of resources and tools to share with folks. Even bad emails help me write posts about what NOT to do!


19. Make people feel good about helping. Give people space to be kind and helpful. If you’re awkward, they’re awkward. Believe in what you ask for. Let them know how much it means to you and how helpful it was. 

20. Say thank you. You can never, ever say thank you enough.

And the closer:

21. Don’t be afraid of hearing “no.” We’re in a culture that’s afraid to say no, and conversely—we’re afraid to ask other people for what we want because we’re also afraid to hear the word “no.”

There’s one person who says no to you more than anyone else, however. When you don’t ask, you’re already selecting “no” as the outcome. Each time you hold yourself back from asking for what you want, or you walk away, silently, you’ve already given yourself the answer that you’re afraid of.

“If you don’t ask, the answer is already no.” (Tweet this!)


What about you? Do you have great tips and strategies (or examples) for how to create winning asks? Do you have specific templates or copy that help you create great asks? Write them in comments alongside + I’ll add them to the post.

Do Less Work By Asking For What You Want

Ever need help with something and don’t know how to ask? Or worse, you think you have to do every step of it yourself?

The other day I was chatting with a good friend of mine. A freelance graphic designer with a decent set of clients, he found himself too busy and overworked–and he began to tinker with the idea of expanding his business. Namely, he wanted to hire someone–a junior designer, or someone to help with some of the sales and management roles in order to help him do more of the creative, expressive work that brought him to the art world in the first place.

One of of the things holding him back, however, was this perceived idea–this expectation–of how long it would take to find this good person.

“I’m just not sure I want to spend another month or two looking for the right person, and then on-boarding them, training them, and developing a working relationship,” he said, frustrated. “That sounds like more time than I’ve got.” Admittedly, his client roster was getting bigger and his time was in more demand–he’d been spending late nights at the computer, drawing and meeting deadlines for his clients.

It was a classic case of “do-it-yourself-iris,” an affliction I’m quite familiar with and still need to take a dose of my own medicine to fix. In this case, there was an ah-ha! moment about how what he thought was holding him back might not be as hard as he was anticipating.

Chances are, five of your friends might know someone–or know someone who knows someone–that can solve your problem.

So I asked him: “Do you think that you know four or five friends that might have already worked with someone who would be good for this job?”

The light went on.

“Well, yes,” he said, “Actually, I’m sure that a few of my friends would know the perfect person.”

Right, I responded. And in fact, even I might even know a few people that would kill for a job like this.

A simple strategy for getting what you want: ask.

I think a lot of us overlook a simple strategy for getting what we want: specifically asking the most influential people around us for help. By “influential,” I don’t mean the most well-connected or well-known; your famous friend or that friend-of-a-friend might not have the bandwidth to answer your message at the moment. Instead, I mean the person or people who can influence you the most. And ideally, the person who knows the person you need.

In just a few minutes, you can email five people and maybe even get what you want within a couple of hours. The work has already been done by someone else: there’s no need to vet a thousand applicants for a graphic design position if three of your good friends can recommend a handful of wonderful people that are actively looking for work.

Entrepreneurs and solo-preneurs often forget that they don’t have to do everything themselves–it’s ironic that what got you here (ie, working incredible hours, figuring it out on your own, teaching yourself the new skills) isn’t what you need to move forward. 

“What got you here / won’t get you there.”  (tweet this)

As your role, life, job, and clients change, so do your strategies for solving them. In many cases, being thrifty and scrappy–and consistently looking for the short-cut that gets you what you want, the fastest–is a great operating play. It’s not cheating to ask for recommendations, it’s efficient. And smart. Because then you can get back to doing the work you want to be doing, quicker. Or finishing your day earlier, so you can have a beer with your friends.

I’ve used this strategy–asking folks in my network for help–in several ways recently:

  • Borrowing a bike for a weekend trip by asking five road biking friends in San Francisco if they had a spare bike. (People who live in San Francisco are often bike enthusiasts).
  • Borrowing a 2009 Mac laptop for some air travel for 4 months because a friend had just purchased a new one and didn’t yet have a plan for the old one (I’ll give it back to him when he sells it or needs it).
  • Finding the best place to get a haircut in San Francisco after going more than a year without getting my hair cut (whoops). No more Yelp. Just ask 3 good folks in they have a recommendation.
  • Asking for advice about how to say “No,” from five of my favorite voices on the internet, including people I’d never met before, by emailing them with a specific client query I kept receiving and asking them if they had a good script for how to say no (and they actually wrote back!).

In each case, I selected people who I thought might know the answer and I asked a few of them directly for help. I was clear about what I wanted, specific in my request, and included a note at the end that gives them permission to decline if they’re too busy.

Do you have a good example of when asking for what you wanted worked out?

Specific email templates for asking:

I’ve been asked to share some of my email templates for asking: here’s one sample email for you to use, borrow, edit and change (and let me know if it works!)

To create a great ask, make sure you include the following information:

  • A specific request for what it is that you want;
  • How long you think the request will take;
  • A chance to opt-out if the person is swamped;
  • Your gratitude and thanks for the help.

For example, here’s a script:

I also included in the message an estimate of how long the request would take:

Dear —-

I’ve got a quick question for you that I think might take you 10 minutes or so to read and respond–my hunch is that you’ve dealt with this before and I’d love your advice (or even a link to someone who has figured this out as well). I’m happy to pay you for your time if this is a longer-answer:

Here’s the situation: I’m looking for a [be specific  about your request] for [this amount of money, time, or energy] and I’m willing to do [list what you can do to make it happen or what you’ve done already].

Personally, I also offer a chance to opt-out, because I like to make sure I’m not imposing by assuming folks will answer my request (you don’t have to do this, but I like to. Here’s that script:

“If you’re too swamped at the moment with your own priorities, feel free to write back “next time!” and delete this email because I know how busy some of you are–no hard feelings. But if this is an easy request that you know how to fill, I’d be darn grateful for a few moments of your time.”  

Remember:

Be clear about what you want.

Be okay with a “no” answer if someone doesn’t have it.

“No” is what you already have, so asking doesn’t put you in a worse position.

You don’t get what you don’t ask for.

Give generously.

Also:

I realize that this is a fortunate vantage point to be in, and isn’t true for everyone around the world, and I want to be clear in recognizing that. For many people, you already know enough people to get what you need. You know far more people than you think. And the world has quite a lot of stuff as it is.

The space between the stuff you want and the people who have it?

Asking for it.